Description:
Villa Paraiso Vacation Rentals manages ~20 luxury vacation homes in Marathon and Key Colony Beach. We're hiring an experienced property manager or realtor to take over our owner relationships and property-care standard, then grow the portfolio. You report directly to the founder and run your book like the business it is.
This is not a coordinator seat. You own outcomes end-to-end: the owner who calls with a problem, the home that has to be guest-ready, the referral that becomes your next signed property.
WHAT YOU'LL OWN
- Owner relationships — single point of contact for homeowners: monthly statements, payouts, revenue conversations, calm and fast problem-solving. Success looks like near-zero owner churn and owners referring their friends.
- Property care & inspections — run inspections, catch wear and damage early, coordinate cleaning and maintenance, verify every turnover. You catch issues, not the guest.
- Operations & quality — own guest-readiness and escalations across the Keys. Keep listings, pricing inputs, and calendars accurate in Guesty, PriceLabs, and Breezeway.
- Growth — sign new owners, turn happy owners into referrals, onboard new homes end-to-end.
YOUR FIRST 90 DAYS
Days 1-30: meet every owner, walk every home, master the stack.
Days 31-60: inspection cadence live, escalations flow through you, first owner wins on the board.
Days 61-90: first new owner signed or referral pipeline built — you're running the book independently.
REQUIREMENTS
- 3+ years in property management, vacation rentals, hospitality, or real estate with real client-relationship or closing experience
- Live in the Florida Keys (Marathon / Middle Keys) with a reliable vehicle
- Strong, calm communicator, obsessive about details
- Comfortable with technology — you'll run an AI-native operations stack
- On-call flexibility for genuine emergencies — you set your hours, but owners and guests come first
NICE TO HAVE
- Active Florida real estate license
- Existing Keys owner or realtor network
- Guesty, Airbnb, VRBO, or Breezeway experience
- A book of owners you could bring with you
COMPENSATION
- Guaranteed base retainer: $40,000-$50,000/year, paid monthly
- Uncapped new-owner commission with accelerators and a signing bonus for each owner you personally bring
- Recurring management-revenue participation on every home you sign, every month it stays
- Equity stake in the company you're helping build
- On-target earnings $75K-$120K+, uncapped
Villa Paraiso Vacation Rentals considers applicants without regard to race, color, religion, sex, national origin, age, disability, veteran status, or any other status protected by law.
Screener questions (Indeed's screening step):
1. Do you currently live in the Florida Keys, or are you able to relocate before starting? → Deal-breaker: Yes
2. How many years of property management, hospitality, or real estate client experience do you have? → Minimum: 3
3. Do you hold an active Florida real estate license? → Not a deal-breaker
Pay: From $75,000.00 per year
Benefits:
- Flexible schedule
- Professional development assistance
Work Location: Hybrid remote in Marathon, FL
